Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

Welcome to the enchanting region of Casselberry, Winter Springs, and Tuscawilla, a hidden gem nestled in the heart of Seminole County, Florida. This vibrant area is renowned for its picturesque landscapes, family-friendly atmosphere, and a strong sense of community, making it an ideal place to call home.

As you explore Winter Springs, you'll be captivated by the lush greenery, scenic parks, and an array of recreational activities that cater to all ages. With its top-rated schools, diverse dining options, and boutique shopping experiences, this area offers a perfect blend of suburban charm and modern conveniences. Whether you’re strolling through the beautiful Central Winds Park or enjoying a weekend at the Winter Springs Town Center, there’s always something to see and do.

One of the most appealing features of homes in this region is the availability of properties with private pools. Imagine stepping into your own backyard oasis, where you can unwind in the sun, host lively barbecues, or enjoy a refreshing swim on a warm Florida day. These homes offer not only a luxurious lifestyle but also a perfect setting for family gatherings and entertaining friends.

With a variety of architectural styles and price points, you’re sure to find a home that fits your needs and desires. From modern designs to cozy retreats, the real estate market here is diverse and inviting.

Discover the charm of Casselberry, Winter Springs, and Tuscawilla, where your dream home with a private pool awaits. Embrace the Florida lifestyle and make lasting memories in this beautiful community!

Newest Casselberrry/Winter Springs / Tuscawilla Homes with Private Pool type

$375,000
4 Beds ⋅ 4 Baths ⋅ Tuscawilla Unit 12 SubDv. ⋅ 32708 Zip Code
Looking for a home, you can make your own while living in it? This 4-bedroom, 3.5-bath single-family home provides an excellent opportunity for an owner-occupant to move in, make updates over time, and build equity while turning the property into their own. Also, a great opportunity for investors, landlords, and buyers looking for a fix-and-hold or value-add project. Located in the established Tuscawilla/Winter Springs area of Seminole County, this home sits on a spacious 0.34-acre lot enclosed by PVC fencing on all four sides in a nice neighborhood. The home features a huge living room, fireplace, ceiling fans throughout, covered porch, attached 2-car garage, skylights, and a screened lanai with pool and jacuzzi. The primary suite includes a double/split vanity with both a tub and separate shower. The spacious yard provides plenty of room to enjoy the outdoor space and make the property your own. Conveniently located near parks, shopping, schools, museums, UCF, Rollins College in Winter Park, Orlando Sanford International Airport, and Orlando International Airport. Whether you're searching for a fixer-upper, handyman special, owner-occupant opportunity, investment property, rental property, landlord opportunity, or value-add project, this property provides plenty of potential to update, improve, and build value over time. Being sold AS-IS.

1625 White Dove Drive, Winter Springs
$930,000
4 Beds ⋅ 3 Baths ⋅ Bentley Club At Bentley Green SubDv. ⋅ 32708 Zip Code
Welcome to 864 Bentley Green Circle, a move-in ready luxury sanctuary situated on a quiet cul-de-sac lot in Winter Springs. Offering 4 bedrooms, 3 full bathrooms, and over 2,200 square feet of meticulously updated living space, this home seamlessly blends sophisticated interior accents with private, resort-style outdoor living. Arrive via a grand circular drive centered around a professionally landscaped island, featuring a newly updated limestone walkway that creates an elegant entryway. Inside, the light-filled open floor plan boasts high ceilings, newly painted walls, transoms, interior glass doors, and smart recessed lighting with nightlight mode. The main living area features a custom black marble gas fireplace and expansive sliding glass doors leading out to the lanai. A formal dining room offers luxury vinyl flooring, custom crown molding, and a statement chandelier, while a dedicated lounge/den provides cozy custom built-ins and window seats. The gourmet kitchen comes complete with granite countertops, tile flooring, newly installed stainless-steel appliances (including a new refrigerator), and convenient access to a laundry area with a recently purchased, large-capacity washer and dryer set. The main-level owner's retreat serves as a true sanctuary, featuring hardwood floors, a sitting area, a built-in electric wall fireplace, space for a coffee station, a spacious walk-in closet, and a completely updated spa bath with a deep soaking tub and oversized glass shower. Upstairs, three additional hardwood-floored bedrooms include one configured as an executive home office with scenic views of the nearby pond and golf course. Step outside into your private backyard oasis featuring a saltwater pool and spa with a newly renovated screen enclosure, updated pool equipment, gas heater, and multi-color lighting. Relax under the custom covered lanai showcasing a real wood ceiling, ceiling fan, and custom recessed lights—complete with included patio furniture and exterior TV. The grounds feature manicured landscaping with lush palm trees, privacy hedges, and a tranquil side-yard "Zen garden" designed to attract butterflies and hummingbirds. Rounding out this exceptional property are dual driveways and a 2-car workshop garage equipped with built-in storage shelving and a 240-amp EV charging station.

864 Bentley Green Circle, Winter Springs
$665,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 14a SubDv. ⋅ 32708 Zip Code
Welcome to this exceptional 4-bedroom, 3-bath pool home with a dedicated office, situated on an oversized corner lot in the heart of Tuscawilla in Winter Springs. Featuring a unique three-way split floor plan, generous indoor and outdoor living spaces, and thoughtful updates throughout, this home offers the perfect combination of functionality, privacy, and Florida living. Step inside through the grand foyer, where a spacious dedicated office sits just off the entry and features French doors, crown molding, beautiful flooring, and plantation shutters. Continue into the inviting living room, highlighted by a brick accent wall, vaulted ceilings, and sweeping views of the pool and lanai. Natural light fills the space through an impressive three-panel sliding glass door that disappears into the wall, creating a seamless transition between indoor and outdoor living—perfect for entertaining. The open floor plan flows into a charming breakfast nook and spacious kitchen featuring an abundance of cabinetry and counter space, stainless steel appliances, and a breakfast bar for casual dining. For larger gatherings and special occasions, the separate formal dining room offers plenty of space and is finished with a beautiful statement chandelier. Privately positioned on one side of the home, the primary suite is a true retreat with vaulted ceilings and its own enclosed Florida room—an incredible space for morning coffee, a reading nook, or peaceful space. The expansive primary bathroom features dual vanities, a brand-new Kohler walk-in shower (2026), and a massive walk-in closet with direct access to the bedroom. The home's thoughtful three-way split design provides exceptional privacy. A second wing features two additional bedrooms and a spacious shared bathroom, while the third wing offers a separate bedroom with its own full bathroom and newly renovated shower (2025)—an ideal setup for guests, extended family, or in-law accommodations. Step outside and experience the Florida lifestyle with a sparkling saltwater pool, new pool heater (2025), and a generous covered lanai designed for year-round entertaining. Beyond the pool, the expansive, fully fenced backyard features new pavers (2024) and plenty of room to relax, play, garden, or entertain. Private and serene, this oversized corner lot provides outdoor space that is increasingly hard to find. Additional highlights include no HOA, a new roof and skylights (2019), new salt cell and pool heater (2024) and brand new A/C (2024). Located in sought-after Seminole County, this home is zoned for Oviedo High School and offers convenient access to everything the Tuscawilla community is known for, including walking trails, public parks, and Tuscawilla Country Club with golf, clay tennis courts, a lap pool, fitness center, and dining. With its oversized lot, three-way split floor plan, private pool, dedicated office, flexible living spaces, and incredible Tuscawilla location, this Winter Springs home delivers the space and lifestyle you've been searching for. Call for your private showing today!

674 Vistawilla Drive, Winter Springs
$499,900
4 Beds ⋅ 3 Baths ⋅ Parkstone SubDv. ⋅ 32708 Zip Code
Virtually Staged. Live the Florida lifestyle in the beautiful gated community of Parkstone! This 4-bedroom, 3-bath pool home offers the perfect combination of comfort, convenience, and resort-style living. Spend sunny afternoons relaxing by your own private screened pool, enjoy morning walks or bike rides along the nearby Cross Seminole Trail, or take advantage of Parkstone’s community pool, tennis and volleyball courts, playgrounds, and lakefront dock on Lake Jesup. Even better, lawn care is included through the HOA, giving you more time to enjoy everything the community has to offer. Inside, the open and inviting layout is designed for both everyday living and entertaining, with spacious gathering areas and easy access to the covered outdoor living and pool area. A downstairs bedroom and full bath provide flexibility for guests, a home office, or multigenerational living, while the spacious primary suite upstairs creates a comfortable private retreat. The home has also been thoughtfully cared for with approximately $5,000 invested in new gutters and an extensive underground drainage system, including underground downspouts and dual French drains. Approximately two tons of river rock, a side-yard walkway, refreshed landscaping in 2026, and refreshed tile grout in all three bathrooms add to the home’s move-in-ready appeal. Whether it’s coffee by the pool, an evening walk through the neighborhood, a bike ride on the trail, or a day enjoying the community amenities, 909 Devon Creek offers more than a home—it offers an easy, active Florida lifestyle.

909 Devon Creek Road, Winter Springs
$439,900
3 Beds ⋅ 3 Baths ⋅ North Orlando Ranches Sec 08 SubDv. ⋅ 32708 Zip Code
Welcome home to this beautifully maintained 3 bedroom, 2.5 bathroom pool home tucked away on a quiet, well mainicured Winter Springs Street, where pride of ownership shines. Designed with entertaining in mind, the spacious great room features a wood burning fireplace and overlooks the backyard oasis, complete with a fully paved pool deck, bar area, and entertaining garden, an incredible space for relaxing or hosting family and friends. Inside, you'll find new luxury vinyl flooring (2026), updated bathrooms, and a cersatile third bedroom featuring a murphy bed and built-ins, perfect for guests, a home office or both. Major improvements include a NEW ROOF (2023), insulated impact windows, and new gutters. And there's NO HOA! Enjoy the freedom of home ownership along with a fantastic Winter Springs location convenient to restaurants, shopping, SR 417, and I-4, plus highly regarded Seminole County Schools.

625 Pearl Road, Winter Springs
$525,000
4 Beds ⋅ 2 Baths ⋅ Oak Forest Unit 6 SubDv. ⋅ 32708 Zip Code
Welcome home to this spacious 4-bedroom, 2-bath pool home located in the highly desirable Winter Springs community! Designed with a functional split-bedroom floor plan, this home offers the perfect balance of privacy, space, and comfortable everyday living. Step inside to soaring vaulted ceilings, abundant natural light, and separate formal living and dining rooms that provide plenty of flexibility for entertaining, working from home, or gathering with family. The heart of the home opens to a large screened lanai and sparkling pool, creating the perfect setting for Florida living year-round. Whether you’re enjoying a quiet morning outside, hosting friends for a weekend barbecue, or cooling off on a summer afternoon, the expansive outdoor living space is sure to become a favorite part of the home. The generously sized lot offers plenty of room to enjoy the outdoors and also features a storage shed with electricity—ideal for a workshop, hobby space, or additional storage. Major improvements offer added peace of mind, including a NEW ROOF, NEW PLUMBING, and NEW WATER HEATER. Best of all, the home is ideally situated in sought-after Winter Springs within walking distance of the area’s schools, making everyday routines incredibly convenient. With its spacious floor plan, beautiful natural light, private pool, large lot, and valuable recent updates, this home offers an incredible opportunity to enjoy everything Winter Springs has to offer!

699 N Endeavour Drive, Winter Springs
$779,000
4 Beds ⋅ 3 Baths ⋅ Tuscawilla Unit 12a SubDv. ⋅ 32708 Zip Code
A rare opportunity awaits in the heart of Tuscawilla. Welcome to 992 Sleeping Rock Court, a distinctive 4 bedroom, 2.5 bath Parade of Homes model pool home offering approximately 2,701 square feet of beautifully updated living space on an oversized .38 acre cul de sac homesite with the exceptional freedom of NO HOA. Designed with character, warmth and impressive architectural detail, this custom Parade of Homes model home immediately stands apart. Striking vaulted tongue and groove cedar ceilings in both the family room and primary suite create a rich, inviting atmosphere, while the beautifully updated wood burning fireplace serves as a dramatic centerpiece to the main living area. The spacious split bedroom floor plan provides privacy and functionality for both everyday living and entertaining. The primary suite feels like a private retreat, showcasing vaulted tongue and groove cedar ceilings, smart LED lighting, a remote controlled smart ceiling fan, custom closet shelving and an ensuite bath overlooking a private atrium. Throughout the home, thoughtful improvements include updated flooring, crown molding, baseboards, interior doors, electrical outlets, faucets and new ceiling fans. The kitchen features 36 inch cabinetry and updated black stainless steel appliances, including a 2025 dishwasher, along with a generous walk in pantry offering excellent storage. A dedicated laundry room, updated hall and half baths, custom closet systems and numerous smart home upgrades add convenience throughout. Step outside and discover an exceptional setting designed for the Florida lifestyle. The expansive covered lanai creates an impressive outdoor living and entertaining space overlooking the private pool with a beautiful natural rock waterfall, mature landscaping and oversized yard. Whether hosting friends, enjoying a quiet evening or relaxing poolside to the sound of the waterfall, this backyard offers the space, privacy and atmosphere that are increasingly difficult to find. The exterior has also received extensive improvements, including new brick pavers, updated fencing, cedar fascia, updated gutters and soffits, refreshed pool equipment with a Pentair pool pump, updated irrigation with a smart WiFi controller and a new mailbox. Major improvements have already been completed, providing tremendous value for the next owner. Updates include a 2019 roof and skylights, 2020 A/C, electrical panel, ductwork repairs and partial replacement, 2023 windows and three sliding glass doors with a Home Depot lifetime warranty, a new front door and a 2024 water heater. Technology and security have also been thoughtfully incorporated throughout the home with fiber internet, CAT8 wiring, a Nest thermostat, Ring doorbell, Nest Yale keypad front entry, keypad garage entry and Ring spotlight video cameras positioned at the front of the property. This home offers the rare combination buyers are searching for: a substantial homesite, a private pool with natural rock waterfall, mature landscaping, architectural character, extensive updates, impressive outdoor living space, Parade of Homes distinction and NO HOA restrictions or monthly HOA dues. It is a distinctive, non cookie cutter property filled with character, thoughtful upgrades and exceptional indoor and outdoor living spaces. Homes offering this combination of size, privacy, improvements, architectural personality and freedom from an HOA are increasingly difficult to find.

992 Sleeping Rock Court, Winter Springs
$644,900
4 Beds ⋅ 3 Baths ⋅ Huntridge SubDv. ⋅ 32708 Zip Code
There’s something about a home that makes everyday life feel a little more like vacation and this Winter Springs pool home delivers just that. Set on a spacious lot in the established Huntridge community, this 4-bedroom, 3-bath home offers nearly 2,850 square feet with room to gather, work, entertain and unwind. Soaring ceilings and abundant natural light create an open, airy feel, while the family room with wood-burning fireplace gives the home a warm, inviting center. A separate office/bonus space adds flexibility for working from home, hobbies or a quiet retreat. Out back, bring vacation home with your own private pool, covered lanai and summer kitchen, an ideal setup for long Florida afternoons, weekend cookouts and evenings spent lingering outside. The primary suite opens directly to the pool area and features a generous walk-in closet and spacious bath. Beyond the house, Winter Springs offers an easygoing, outdoor-focused lifestyle with nearby Trotwood Park, miles of walking and biking along the Cross Seminole Trail, Tuscawilla Country Club, and shopping and dining around Winter Springs Town Center and Tuskawilla Road.

248 Huntridge Way, Winter Springs
$549,000
4 Beds ⋅ 3 Baths ⋅ Oak Forest Unit 8 SubDv. ⋅ 32708 Zip Code
Spacious 4 bedroom, 3 bathroom pool home off of Tuskawilla Rd! This home features two story ceiling in the formal living and dining room. The staircase and second story walkway over look the entrance and formal areas. The family room has a fireplace and is joined with the kitchen. On the first floor are also three large bedrooms, two of the bedrooms have attached baths. The primary bedroom is upstairs and has double walk in closets, and an oversized en suite bathroom. The pool has a screen enclosure and the yard is fenced. Roof replaced in 2022, complete Replumb ins 2023.

1142 Oday Drive, Winter Springs
$425,000
3 Beds ⋅ 2 Baths ⋅ Country Club Village Unit 2 SubDv. ⋅ 32708 Zip Code
Welcome to this beautifully maintained 3-bedroom, 2-bath POOL home nestled on a quiet, tree-lined street in the highly sought-after Country Club Village of Tuscawilla. This inviting home offers a versatile floor plan ideal for both everyday living and entertaining, with volume ceilings, abundant natural light, and attractive, low-maintenance tile and luxury vinyl plank flooring throughout. The spacious living and dining areas provide wonderful flexibility and can easily be arranged to complement your lifestyle. At the heart of the home, the kitchen overlooks the dinette and family room and features stainless steel appliances, ample prep and storage space, pull-out drawers, a built-in pantry and built-in wine rack. Its thoughtful location also offers possibilities to open or expand the kitchen toward the rear of the home, creating an even greater connection to the outdoor living and pool area. A charming greenhouse window in the dinette is perfect for growing fresh herbs or displaying your favorite plants. The spacious owner's suite provides a relaxing retreat with direct access to the back porch, a beautifully updated shower and vanity with granite countertop, an oversized window overlooking the atrium, and generous closet space. Two sizable secondary bedrooms are located toward the front of the home, with one offering direct access to the charming atrium. Step outside and enjoy your morning coffee or unwind at the end of the day on the private back patio overlooking the sparkling pool and hot tub, all tucked behind a privacy wall to create your own peaceful outdoor retreat. The pool screen was replaced in 2022 for added peace of mind. The OVERSIZED two-car garage is another standout feature, offering an extended workshop area with ample room for a golf cart, along with built-in shelving, attic stair access and a convenient rear-exit door. Hot water heater replaced Sept 2026. Country Club Village offers the perfect combination of a peaceful neighborhood setting and exceptional convenience. Located adjacent to Tuscawilla Country Club, optional memberships provide access to golf, tennis, fitness facilities, social activities, clubhouse amenities and more. Enjoy nearby parks and nature trails, highly rated Seminole County schools, shopping and dining, along with convenient access to UCF, Seminole State College, Orlando Sanford International Airport, Orlando International Airport and major roadways 417, 408, 528 and I-4. Don't miss the opportunity to make this exceptional Tuscawilla pool home your own—schedule your private showing today!

1162 E Winged Foot Circle, Winter Springs
$510,000
3 Beds ⋅ 2 Baths ⋅ Eagles Watch Ph 1 SubDv. ⋅ 32708 Zip Code
Property is well maintained, had been owned by a former major league baseball prayer. Adjacent to a nice secluded pond. The pool and lanai area is wonderful for quiet sitting, meditation, reading and then jump into the pool for a refreshing dip. The subdivision is one minute from a convenience store and access to Rt 417 highway to all parts of Central Florida. Spacious master bedroom with very big walk-in closet. This is in move-in condition subject only to your color decorations. Part of the Tuscawilla Master Community !!

133 Redtail Place, Winter Springs
$539,000
4 Beds ⋅ 2 Baths ⋅ Oak Forest SubDv. ⋅ 32708 Zip Code
Beautiful pool home in Oak Forest. NEW ROOF, NEW SOD Coming soon.. NEW INTERIOR PAINT and VINYL FLOORS. Gorgeous 42" kitchen cabinets with granite counters and large Island with seating and tiled backsplash. Both bathrooms have beautiful vanities and glass tiles and granite counters. Fourth bedroom has been turned into an office but could be converted back into a bedroom by adding a closet. Tall ceilings, tile and Vinyl floors throughout, open floorplan and neutral colors complete the interior package but there's more! Brick paver front entry and large screened pool area make this a home you won't want to miss. New SOD and landscaping will be done soon.

1114 Seafarer Lane, Winter Springs
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